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Triethylamine → HCID 59514495, compound

HRID 1159671
Notes
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Reaction equation

HRID 1159671 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:12]=[C:11]([N:13]([CH3:15])[CH3:14])[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:9]([N:21]([CH3:23])[CH3:22])[N:8]=2)=[CH:4][CH:3]=1.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1.C(N(CC)CC)C>ClCCl>[CH3:23][N:21]([CH3:22])[C:9]1[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:11]([N:13]([CH3:15])[CH3:14])[N:12]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[C:31]3[CH:35]=[CH:36][C:28]([C:27]([F:26])([F:37])[F:38])=[CH:29][CH:30]=3)=[CH:25][CH:24]=2)[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 59514565HCID 59514565, compound

Product 1

HCID 59514495HCID 59514495, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl [2-(4-aminobenzyl)-4,6-bis(dimethylamino)pyrimidin-5-yl]acetate (4.00 g, 11.65 mmol) in dichloromethane (120 mL) was treated with 4-trifluoromethylbenzoyl chloride (2.92 g, 13.98 mmol) and triethylamine (3.54 g, 34.94 mmol). After stirring for 1 hour at room temperature, the reaction mixture was partitioned between water and chloroform and the aqueous layer was extracted with chloroform. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude product as a yellow colored solid which was recrystallized from methanol to give methyl [4,6-bis(dimethylamino)-2-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)pyrimidin-5-yl]acetate (4.34 g, 73%) as a white solid.

Workup

  1. customthe reaction mixture was partitioned between water and chloroform
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product as a yellow colored solid which
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-e1b83e0e9a0e4ba9b165a07ecb4ec7be
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07812160B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes